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A Novel, One‐Pot Synthesis of Novel 3F, 5F, and 8F Aromatic Polymers
Author(s) -
Diaz Adan M.,
Zolotukhin Mikhail G.,
Fomine Serguei,
Salcedo Roberto,
Manero Octavio,
Cedillo Gerardo,
Velasco Victor M.,
Guzman Maria T.,
Fritsch Detlev,
Khalizov Alexei F.
Publication year - 2007
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200600656
Subject(s) - superacid , polymer , biphenyl , electrophilic aromatic substitution , friedel–crafts reaction , polymer chemistry , ether , benzene , chemistry , diphenylmethane , terphenyl , nucleophilic aromatic substitution , electrophilic substitution , organic chemistry , condensation polymer , naphthalene , nucleophilic substitution , catalysis
A series of novel, linear, soluble, high‐molecular‐weight, fluorinated aromatic polymers has been obtained for the first time using a superacid‐catalyzed polyhydroxyalkylation reaction of fluorinated carbonyl‐containing compounds: 1,1,1,‐trifluoroacetone ( 1 ), 2,2,2‐trifluoroacetophenone ( 2 ), 2,3,4,5,6,‐pentafluorobenzaldehyde ( 3 ), and octafluoroacetophenone ( 4 ) with aromatic hydrocarbons such as biphenyl ( a ), phenyl ether ( b ), terphenyl ( c ), and 4,4′‐diphenoxybenzophenone ( d ). These Friedel‐Crafts‐type aromatic electrophilic substitution reactions are performed at room temperature in trifluoromethane sulfonic acid or in its mixtures with dichloromethane. The polymers obtained are soluble in common organic solvents, and colorless transparent films could be cast from the solutions. 1 H and 13 C NMR analyses of the polymers synthesized reveal their linear, highly regular structure. The polymers also possess high thermostability.